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9. Robert Citron (Loss: $1.7 billion)

Robert Lafee Citron was the treasurer and tax controller of the Orange County, California. Citron has direct control on the handling of the Orange Country fund and he went to the repo market to leverage the fund. In December 1994, the Credit Suisse First Boston blocked his rolling over repos and the Orange County filed for bankruptcy protection. Citron pled guilty for numerous felony counts and the bankruptcy caused the loss of jobs for 3,000 public employees. He was ordered to perform 1000 hours of community services and serve 5 years of supervised probation. Citron never spent any time in prison.

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